DE637909C - Process for the production of higher alcohols from ethyl alcohol - Google Patents
Process for the production of higher alcohols from ethyl alcoholInfo
- Publication number
- DE637909C DE637909C DEA63351D DEA0063351D DE637909C DE 637909 C DE637909 C DE 637909C DE A63351 D DEA63351 D DE A63351D DE A0063351 D DEA0063351 D DE A0063351D DE 637909 C DE637909 C DE 637909C
- Authority
- DE
- Germany
- Prior art keywords
- alcohol
- ethyl alcohol
- production
- higher alcohols
- amount
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims description 18
- 235000019441 ethanol Nutrition 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 11
- 150000001298 alcohols Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000002184 metal Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 3
- 239000012190 activator Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- 239000000292 calcium oxide Substances 0.000 description 2
- 235000012255 calcium oxide Nutrition 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
- C07C29/34—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups by condensation involving hydroxy groups or the mineral ester groups derived therefrom, e.g. Guerbet reaction
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Es ist bereits bekannt, durch Behandeln von Äthylalkohol mit Katalysatoren höhere Alkohole herzustellen. Bei diesem Verfahren entstehen aus dem Alkohol zunächst einmal Acetaldehyd und dann durch Kondensation des Acetaldehyds Stoffe mit höherem Kohlenstoffgehalt. It is already known by treating higher ethyl alcohol with catalysts Manufacture alcohols. In this process, the alcohol is first created Acetaldehyde and then, by condensation of the acetaldehyde, substances with a higher carbon content.
Diese Verfahren weisen den Nachteil auf, daß infolge der großen Reaktionsfähigkeit des Acetaldehyds neben dem Hauptprodukt Butylalkohol in verhältnismäßig großen Mengen unerwünschte Nebenprodukte, wie Essigsäure, Acetaldehyd und Butylaldehyd, entstehen. Infolgedessen haben sich diese Verfahren als unwirtschaftlich erwiesen.These methods have the disadvantage that due to the high reactivity of acetaldehyde, in addition to the main product butyl alcohol, in relatively large quantities unwanted by-products, such as acetic acid, acetaldehyde and butylaldehyde, are formed. As a result, these methods have proven to be inefficient.
Man hat nun weiter vorgeschlagen, Äthylalkohol unter hohem Druck in Gegenwart von Oxyden alkalischer Erden und dehydrierend wirkenden Metallen höheren Temperaturen zu unterwerfen. Bei diesem Verfahren werden etwas höhere Ausbeuten erzielt. Dieses Verfahren entspricht aber immer noch nicht den Bedürfnissen der Technik.It has now been proposed to use ethyl alcohol under high pressure in the presence of Oxides of alkaline earths and dehydrating metals at higher temperatures to subjugate. Somewhat higher yields are achieved in this process. This However, the process still does not meet the needs of technology.
Es hat sich nun gezeigt, daß sich eine wesentliche Erhöhung der Ausbeute dadurch erzielen läßt, wenn man das Verfahren in Gegenwart kleiner als Aktivatoren wirkender Metallmengen, insbesondere Kupfer, ausführt, und zwar verwendet man Mengen bis zu etwa 50/0. Auf diese Weise gelingt es ohne weiteres, 50 bis 55 o/o des angewendeten Alkohols in höhere Alkohole, insbesondere Butylalkohol, überzuführen. Das Oxyd wirkt als wasserabspaltendes Mittel.It has now been shown that this results in a substantial increase in the yield can be achieved if the process in the presence of smaller activators acting Amounts of metal, especially copper, executes, using amounts up to about 50/0. In this way it is easily possible to use 50 to 55 o / o of the alcohol used transfer higher alcohols, especially butyl alcohol. The oxide acts as a dehydrating agent Middle.
Die Reaktion geht nach der FormelThe reaction goes according to the formula
2 CH3CH2OH = C3H7CH2OH -f- H2O2 CH 3 CH 2 OH = C 3 H 7 CH 2 OH -f- H 2 O
vor sich.in front of you.
Es werden bei diesem Verfahren als End-, produkte neben Butylalkohol Hexyl- und Octylalkohol erhalten. Aldehyde, Ketone, Säuren oder Ester können in dem Reaktionsprodukt nicht nachgewiesen werden. In this process, the end products, in addition to butyl alcohol, are hexyl and Obtained octyl alcohol. Aldehydes, ketones, acids or esters cannot be detected in the reaction product.
ι kg Äthylalkohol wird in einem Autoklaven mit 400 g CaO und 10 g Kupfer auf z. B. 3000 erhitzt. Das erhaltene Reaktionsprodukt wird bei dieser Temperatur aus dem Autoklaven abgetrieben und der Kalk dadurch wieder reaktionsfähig gemacht, daß die letzten Reste des Reaktionsproduktes bei 3500 abgetrieben werden.ι kg of ethyl alcohol is in an autoclave with 400 g of CaO and 10 g of copper on z. B. 300 0 heated. The obtained reaction product is driven off at this temperature from the autoclave and the lime rendered again reactive that the last remnants of the reaction product are stripped at 350 0th
Die Ausbeute an Butyl-, Hexyl- und Octylalkohol beträgt 50 bis 55 o/o des angewandten Alkohols. 350g Alkohol werden als 8oO/oiger Alkohols wiedergewonnen.The yield of butyl, hexyl and octyl alcohol is the alcohol used 50 to 55 o / o. 350 g of alcohol are recovered as 80% alcohol.
Das hier geschilderte diskontinuierliche Verfahren läßt sich auch kontinuierlich durchführen, wenn man Alkoholdämpfe, die auf höhere Temperaturen, beispielsweise 3000, vorgewärmt sind, bei einem Druck von etwaThe discontinuous process described here can also be carried out continuously if alcohol vapors, which are preheated to higher temperatures, for example 300 0 , at a pressure of about
*) Von dem Patentsucher sind als die Erfinder angegeben worden:*) The patent seeker indicated the following as the inventors:
Dipl.-Ing. Max Steinschneider und Dr.-Ing. Wilhelm Ziroff in Aschaffenburg.Dipl.-Ing. Max Steinschneider and Dr.-Ing. Wilhelm Ziroff in Aschaffenburg.
28o bis 3Ρ°. Atm. über Ätzkalk in Gegenwart
von Metallen, insbesondere Kupfer, leitet. In diesem Falle ist es zweckmäßig, das Überleiten
des Alkohols von Zeit zu Zeit zu unterbrechen und den Kalk durch Erhitzen
3 5 o° wieder reaktionsfähig zu machen.28o to 3Ρ °. Atm. over quicklime in the presence of metals, especially copper. In this case it is advisable to interrupt the passage of the alcohol from time to time and the lime by heating
3 5 o ° to be able to react again.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA63351D DE637909C (en) | 1931-09-10 | 1931-09-10 | Process for the production of higher alcohols from ethyl alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA63351D DE637909C (en) | 1931-09-10 | 1931-09-10 | Process for the production of higher alcohols from ethyl alcohol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE637909C true DE637909C (en) | 1936-11-05 |
Family
ID=6943176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA63351D Expired DE637909C (en) | 1931-09-10 | 1931-09-10 | Process for the production of higher alcohols from ethyl alcohol |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE637909C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2645668A (en) * | 1951-10-01 | 1953-07-14 | Phillips Petroleum Co | Condensation of alcohols in the presence of calcium oxide |
-
1931
- 1931-09-10 DE DEA63351D patent/DE637909C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2645668A (en) * | 1951-10-01 | 1953-07-14 | Phillips Petroleum Co | Condensation of alcohols in the presence of calcium oxide |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE637909C (en) | Process for the production of higher alcohols from ethyl alcohol | |
| DE2157307A1 (en) | Process for the production of acetone | |
| DE2105014B2 (en) | PROCESS FOR THE PRODUCTION OF 2,5DIMETHYL-2,3-DIHYDROFURAN-4-OXY-3-ON | |
| CH406189A (en) | Process for the production of pure, unsaturated, aliphatic nitriles | |
| DE927626C (en) | Process for the preparation of ª-Aethyl-ª-isopropylacrolein | |
| DE964237C (en) | Process for the preparation of oxidation products from cyclohexane and its homologues | |
| DE1593005C3 (en) | Process for the production of methyl acrylate or methyl or ethyl methacrylate | |
| DE523189C (en) | Process for the preparation of esters from acid amides and alcohols | |
| DE1418067A1 (en) | Process for the preparation of trialkyladipic acids | |
| DE1124932B (en) | Process for the preparation of 2,2,4-trimethyl-1,3-pentanediol | |
| DE1102142B (en) | Process for the preparation of 1: 1 adducts of cyclododecatrienes (1, 5, 9) and / or trivinylcyclohexane with maleic anhydride or with esters of maleic acid and / or fumaric acid | |
| DE2064505C3 (en) | Process for the preparation of ethyl bromoacetate | |
| DE483454C (en) | Process for the preparation of concentrated acetic acid and other lower members of the fatty acid series | |
| DE229854C (en) | ||
| DE844293C (en) | Process for the preparation of aliphatic aldehyde carboxylic acids | |
| DE704298C (en) | Process for the production and recovery of isopropyl acetate | |
| DE958196C (en) | Process for the production of terephthalic acid or its potassium salts and their esters | |
| DE1518566B2 (en) | ||
| DE1518572C (en) | Process for the preparation of the acrylic acid and methacrylic acid monoesters of alkanediols | |
| DE804563C (en) | Process for the preparation of esters of butanediol-1, 4-one-2 and its homologues | |
| DE857951C (en) | Production of ª ‡ -substituted acroleins | |
| DE863651C (en) | Process for purifying trimethylolpropane | |
| DE838000C (en) | Process for the preparation of carboxylic acid esters of aliphatic ªÏ-chloro alcohols | |
| DE500504C (en) | Process for the preparation of resins | |
| DE735637C (en) | Process for the preparation of aliphatic monocarboxylic acids dihalogenated in the ª ‡, ª ‰ position |